Aminophosphonate
{{Short description|Class of organophosphorus compounds}}
Aminophosphonates are organophosphorus compounds with the formula (RO)2P(O)CH2NR2. These compounds are structural analogues of amino acids in which a carboxylic moiety is replaced by phosphonic acid or related groups.{{cite journal|volume=350|issue=9|year=2008|pages=1195–1208|title=Catalytic Enantioselective Hydrophosphonylation of Aldehydes and Imines|author=Pedro Merino|author2=Eugenia Marqués-López|author3=Raquel P. Herrera|journal=Advanced Synthesis & Catalysis|doi=10.1002/adsc.200800131|hdl=10261/114023|hdl-access=free}} Acting as antagonists of amino acids, they inhibit enzymes involved in amino acid metabolism and thus affect the physiological activity of the cell. These effects may be exerted as antibacterial, plant growth regulatory or neuromodulatory. They can act as ligands, and heavy metal complexes with aminophosphonates have medical applications.{{cite journal|last1=Tušek-Božić|first1=LJ|title=Aminophosphonate metal complexes of biomedical potential|journal=Current Medicinal Chemistry|date=2013|volume=20|issue=16|pages=2096–117|pmid=23432587|doi=10.2174/0929867311320160004}}
Phosphonates are more difficult to hydrolyse than phosphates.{{cite journal|last1=Orsini|first1=F|last2=Sello|first2=G|last3=Sisti|first3=M|title=Aminophosphonic acids and derivatives. Synthesis and biological applications.|journal=Current Medicinal Chemistry|date=2010|volume=17|issue=3|pages=264–89|pmid=20214568|doi=10.2174/092986710790149729}} Some aminophosphonates degrade to aminomethylphosphonic acid.{{cite journal | last=Schwientek | first=M. | last2=Rügner | first2=H. | last3=Haderlein | first3=S.B. | last4=Schulz | first4=W. | last5=Wimmer | first5=B. | last6=Engelbart | first6=L. | last7=Bieger | first7=S. | last8=Huhn | first8=C. | title=Glyphosate contamination in European rivers not from herbicide application? | journal=Water Research | volume=263 | date=2024 | doi=10.1016/j.watres.2024.122140 | page=122140| url=https://www.researchsquare.com/article/rs-3917957/latest.pdf }}
Preparation
Aminophosphonates are often prepared by hydrophosphonylation, usually the condensation of imines and phosphorous acid. In the Pudovik reaction or Kabachnik–Fields reaction, the esters of phosphorous acid are employed, e.g. diphenylphosphite. Because these compounds are of pharmaceutical interest, methods have been developed to induce these additions asymmetrically.{{cite journal|volume=6|issue=9|year=2016|pages=5915–5924|title=Synthesis of new α-aminophosphonate derivatives incorporating benzimidazole, theophylline and adenine nucleobases using L-cysteine functionalized magnetic nanoparticles (LCMNP) as magnetic reusable catalyst: evaluation of their anticancer properties|author=Foroogh Bahrami|author2=Farhad Panahi|author3=Ali Khalafinezhad|journal=RSC Advances|doi=10.1039/C5RA21419J |bibcode=2016RSCAd...6.5915B|hdl=10261/114023}}{{cite journal|doi = 10.1021/jm200587f|title = Remarkable Potential of the α-Aminophosphonate/Phosphinate Structural Motif in Medicinal Chemistry|year = 2011|last1 = Mucha|first1 = Artur|last2 = Kafarski|first2 = Paweł|last3 = Berlicki|first3 = Łukasz|journal = Journal of Medicinal Chemistry|volume = 54|issue = 17|pages = 5955–5980|pmid = 21780776}}
Examples
Aminomethylphosphonic_acid.svg|Aminomethylphosphonic acid (AMPA), the simplest possible aminophosphonate.
Glyphosate.svg|Glyphosate, a common though contentious herbicide
ATMP.png|ATMP is used in water treatment as antiscalant{{cite journal | last=Tang | first=Yongming | last2=Yang | first2=Wenzhong | last3=Yin | first3=Xiaoshuang | last4=Liu | first4=Ying | last5=Yin | first5=Pengwei | last6=Wang | first6=Jintang | title=Investigation of CaCO3 scale inhibition by PAA, ATMP and PAPEMP | journal=Desalination | volume=228 | issue=1-3 | date=2008 | doi=10.1016/j.desal.2007.08.006 | pages=55–60}}
EDTMP.png|EDTMP, a chelating agent. Its 153Sm complex (Quadramet) is used in the treatment of cancer
DTPMP.png|DTPMP